Ammonium Chloride → 5-(2-Methylprop-1-en-1-yl)pyridine-2-carbaldehyde

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a 2.0M butylmagnesium chloride tetrahydrofuran solution (11.2 mL) was diluted with tetrahydrofuran (200 mL). The reaction solution was cooled to −10° C., a 1.6M n-butyllithium hexane solution (28.1 mL) was added dropwise, and the mixture was stirred at −10° C. for 10 min. To the reaction solution was added dropwise a solution (50 mL) of 2-bromo-5-(2-methylprop-1-en-1-yl)pyridine (11.9 g) in tetrahydrofuran, and the mixture was stirred at −10° C. for 30 min. To the reaction solution was added N,N-dimethylformamide (8.65 mL), and the mixture was stirred at −10° C. for 3 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:99-10:90, volume ratio) to give the title compound (7.47 g, yield 83%) as a pale-yellow oil.

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